


How Not to Do a Dare

by cenotaphy



Series: Shortfic Requests [1]
Category: Supernatural
Genre: Alternate Universe - High School, Athlete Castiel (Supernatural), Blindfolds, Castiel knows what he wants, Cheerleader Dean Winchester, Dean in a Skirt, Dean knows what he wants, M/M, One Night Stands, Openly Bisexual Dean Winchester, Openly Gay Castiel (Supernatural), Party, Porn With Plot, Samulet (Supernatural), Sex, Shy Dean Winchester, Top Castiel/Bottom Dean Winchester, Truth or Dare, Very little angst!, mostly plot if I'm being honest
Language: English
Status: Completed
Published: 2019-05-07
Updated: 2019-05-07
Packaged: 2020-02-27 14:09:47
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,941
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18740632
Author URL: https://archiveofourown.org/users/cenotaphy/pseuds/cenotaphy
Summary: Castiel's the star quarterback of the high school football team and the most popular guy in school. Dean's just a nobody cheerleader who isn't even supposed to be at this party and who definitely shouldn't have agreed to this stupid dare. In fact, he's not even going to do it.(At least, that's what he thinks.)





	How Not to Do a Dare

**Author's Note:**

  * For [hello_goodbye_number4](https://archiveofourown.org/users/hello_goodbye_number4/gifts).



Dean closes the door softly behind him, swallowing hard at the gentle click of the knob. The bedroom isn't as dark as he'd expected it would be; the window blinds are up and an orange-red glow from the streetlamp beyond pours in, painting a ruddy halo around the motionless form stretched out on the narrow bed.

Castiel Novak. High school senior, straight-A student, beloved quarterback of the football team, shoe-in for prom king this year, and taking a fucking nap at his own goddamn house party.

And, Dean thinks ruefully, then there's him. Dean Winchester. Edging closer to the bed in his stupid cheerleading uniform, which he didn't even have time to wash after the game today. He'd only worn it so that he'd have a better chance of getting into this dumb party, which is so jazzed on team spirit that when he, Benny and Jo all showed up in full regalia (Benny and Jo in their dorky band getups and Dean in a pleated skirt that, frankly, makes his ass look _great_ ) the crowd inside only roared with drunken delight and yanked them inside.

Dean hovers by the bedside and stares down at Castiel, who looks, if possible, even more gorgeous up close. Dean's never even spoken to Castiel, only watched him hungrily from afar during games and practices. Now here the guy is, totally oblivious and an arm's length away, in all his tousled, artless, shirtless glory. Castiel is stretched out on his back on top of the patterned quilt with his hands tucked behind his head; even asleep, the corner of his mouth looks like it's tugged up in a half-smirk, the cocky expression of someone who knows they exist at the top of the food web.

Dean sighs and tugs fretfully at his amulet, the cool weight a familiar comfort against his fingertips. Well, why _shouldn't_ Castiel be smug? Being the most popular guy in school has its perks. Castiel could have any guy he wants—probably any girl he wants, too, not that Castiel makes any secret of _not_ being interested in girls. And Dean? Dean's just a stupid dork who can do a decent backflip and who's half-regretting all the life choices that have led him here, sneaking through a stranger's bedroom on a dare.

("Until someone comes," Jo said. "Doesn't matter which of you."

"Let's be real." Benny snickered into his cup. "S'gonna be Dean.")

Dean snorts and turns away from the bed. Benny and Jo dared him fifty bucks each, which is a not insubstantial amount of money and enough, in their minds, to tempt Dean. Except Benny and Jo are also idiots and all they wanted for proof were Castiel's boxers. Which...this is Castiel's bedroom, after all. Not like there aren't any other pairs lying around. Dean picks his way across the junk scattered on the carpet, towards the open closet door.

Not that he'd _mind_ , Dean thinks, stealing a glance over his shoulder at the various planes and angles of Castiel's body, the unkempt tangles of his feathery-dark hair. Just not while the dude is sleeping, is all. And since (regardless of how often Dean's fantasized about it) there's no way an _awake_ Castiel would ever throw someone like Dean a second glance, that basically means...never. Oh well.

Dean spies the laundry hamper, sitting unguarded just inside the closet door. The entire closet smells of something sweet and sharp that he assumes is Castiel's deodorant or maybe just _Castiel_ and as he rummages in the hamper to pull out a discarded pair of boxers he has to fight the sudden urge to press them to his face. What's _wrong_ with him?

He straightens, boxers crushed in one hand, and makes it three steps toward the bedroom door when a gravelly voice says from behind him, "You're just gonna leave?"

Dean freezes.

Slowly, he turns.

Castiel hasn't moved. His _eyes_ are still closed. But his smirk looks a little wider.

"You were awake this whole time?" Dean accuses.

The smirk grows even more, and _god_ , is that a flash of teeth? Dean swallows, his throat suddenly bone-dry.

"You're the one sneaking into my bedroom instead of enjoying yourself downstairs at my party," says Castiel amicably. "What'd you get dared to do, steal one of my socks?"

"Why would I want one of your _socks_?"

Castiel arches a perfect eyebrow at the ceiling and drawls, "Come on, you don't think you could make good use of one of my socks?"

"Gross."

"Says the guy who got dared to go through my dirty laundry, apparently."

"I got dared to _fuck_ you, you asshole," Dean snaps, and instantly regrets it. He swivels his head toward the door, his whole body tensing as he waits for Castiel to order him out or come at him swinging. It's a small bedroom. He's _pretty_ sure he can make it to the door before Castiel can reach him.

Castiel does move, but only to stretch lazily on the bed, his bare feet glowing in the orange light as he stretches and then flexes his calves and settles more comfortably into the pillows.

"Well. You gonna do it?"

" _No_. You were asleep."

"I'm awake now."

Dean sputters. "I—no, I—"

"Come on," says Castiel. He moves one hand to skate his palm down his bare chest, his stomach, the fingers just barely grazing his waistband, before tucking it back into position behind his head and tipping his chin up toward the ceiling. "I'd be a terrible host if I got between a man and his dare."

Dean doesn't _remember_ dropping the boxers, but they're certainly no longer in his hand. Before he quite realizes what's happening, his feet are carrying him back towards the bedside. Castiel doesn't move—keeps his hands behind his head and his closed eyes pointed directly at the ceiling.

"Only if, y'know." The slightest intimation of a shrug from Castiel. "If you want."

And fuck, Dean _does_ want. He's hard already. And he's pretty sure Castiel knows it.

"Are you," Dean swallows. "Are you gonna look?"

Castiel cocks his head very slightly, the gesture somehow every bit as sincere as all the expressions before were smug. "Do you want me to look?" he says carefully.

"No," Dean blurts, not quite sure why that's his answer, unless it's that he's only himself and Castiel is _all of that_ and maybe anonymity is the best safeguard he has.

The smirk is back, deepening into a slow grin, and Castiel slowly stretches one hand out along the pillow to his bedside table, rummaging in its single drawer and pulling something out. A fucking _blindfold_.

"Jesus," Dean breathes.

Castiel tugs the blindfold down over his own eyes and _tsks_ , and how a sound that's usually the purveyance of elderly librarians can sound so hot coming from that mouth, Dean has no idea. "That's the last time you'll say a name in here that isn't mine."

Basically all the blood in Dean's body rushes downward. Brain cells, exeunt stage dick. He swallows hard, one more time, and _what the hell_ , he's going for it.

He shimmies out of his underwear and clambers onto the bed to straddle Castiel. Slowly, holding his breath, trying not to think too much about how improbable this is, how _insane_ , he grinds down. Under the atrociously garish pants, the same vivid shade of school spirit as Dean's skirt, Castiel is sizable, and as hard as Dean is.

Castiel reaches down and grips Dean by the hips, pulling him closer. Dean leans down and hesitates for a bare moment before closing his mouth over Castiel's. The satiny fabric of the blindfold bumps against his eyebrow. He bites down on Castiel's bottom lip, gently, and is rewarded with a soft sound of pleasure.

"You're not going to break me," Castiel breathes into Dean's mouth, and the next thing Dean knows Castiel is kissing him back, hard, their teeth clinking briefly together before Castiel's tongue is licking its way into his mouth. Castiel's mouth is soft and his tongue is a reaching, _insistent_ heat, and all the while Castiel's grip is like iron on Dean's hips, pulling him, holding him. Dean grinds down and Castiel hisses into Dean's open mouth and drives his hips up, lifting— _oh, god_ —Dean into the air until his weight is just barely resting on his knees.

Castiel skims his hands upward, running them over Dean's shirt for a minute before curling his fingers under the hem and dragging it up to Dean's shoulders. Dean barely has time to shrug the whole thing off and fling it onto the floor before Castiel has his hands on Dean's biceps and is pulling him in, down, _in_. Their mouths lock together again as Castiel drags his fingers up and down Dean's bared spine, blunt nails scraping the skin without breaking it. Dean hums his pleasure and reaches out to tangle his hand in Castiel's hair. The steely-hot line of Castiel's dick is pressed right into the crease of his thigh, and when Dean props himself on one elbow and reaches down to it with his freed hand, Castiel makes a sharp, hungry noise and pulls back the barest half-inch.

"Lube," Castiel pants. " _Drawer_."

Dean leans over, scrabbling in the drawer. Castiel turns his head and mouths at Dean's hand where it's braced on the mattress by his head. "Hurry up," he hums, sucking a noisy kiss into the base of Dean's thumb.

It seems to take forever but Dean finally gets hold of a foil condom packet and the small bottle of aforementioned lube. He coats his fingers and reaches below the hem of his skirt, hissing a little at the cold as he opens himself up. Castiel, meanwhile, already has the condom in hand and is rolling it onto himself with surprising dexterity considering the blindfold.

Dean scoots up and feels the head of Castiel's cock pressing against his entrance. He braces the very tips of his fingers on Castiel's chest and prepares to lower himself, but Castiel suddenly reaches out and has his hips immobilized once more in that merciless grip.

"I don't want to hurt you," Castiel says, and there it is again, that gentle earnestness, and Dean's heart experiences a sweet pang entirely separate from the baser sensations preoccupying his dick.

"You won't," he says, and tugs Castiel's fingers off his hips, twining them with his own as he sinks _down_ , a brief tight sharpness, a slow drag of heat inside him, and _there_. Castiel tips his head back, exposing the lovely clean line of his throat, and groans. Dean rocks his hips gently, then harder. Castiel groans again, softer, and his hand flits up to lightly cup Dean's chin.

"Beautiful," Castiel whispers at the ceiling, at _Dean_ , and then he pushes up into Dean, and then again, and again, faster, until he's setting a steady pace in perfect rhythm, hitting a spot that lights up a white fire in Dean's veins. Dean hears bitten-off sounds of pleasure coming from his own mouth, but he barely recognizes his own voice, the wrecked abandon of the sounds he's making. Castiel adjusts his hands, the fingers splayed over Dean's hips, under the skirt, digging into the skin, and he never varies the cadence, doesn't speed up or slow down just _moves_ in Dean, just moves and pulls that concentrated lightning out of every cell of Dean and drags it into a single cresting point—

" _Castiel_ ," Dean gasps. "Castiel—Cas—"

Without warning, Castiel brings one hand to his mouth and licks his palm, and then he has Dean in hand. Without breaking the pace of his thrusting hips, he strokes Dean once, twice, three times, and then Dean is crying out and spilling onto Castiel's fingers, onto his belly, onto that orange-lit skin. He's barely aware of Castiel's muscles going taut, of Castiel gritting out a desperate, formless sound between clenched teeth as his hips punch upwards one last time. Their bodies hold the position in shaking tandem for a long, blissfully-stretched second, before Castiel's hips finally drop back onto the blanket.

Dean follows him down, gasping a little, his chin dropping to his chest as he feels his heart rate slow. "Holy shit," he pants when he can manage to speak.

"Quite," Castiel agrees. He lets go of Dean's hips at last, but doesn't pull his hands away; instead one moves to Dean's back, rubbing lazy circles, and one actually moves to the back of Dean's head, gently scratching his hair.

The tenderness of the gesture startles a few sparks of life back into Dean's satiated brain. He blinks hazily down at Castiel and is hit by the sudden urge to kiss him again, long and slow and lazy, and maybe pull off the blindfold and see if Castiel's eyes are as blue up close as they look out on the field in afternoon sunlight. He drops his gaze after a moment, suppressing the desire. Registering the release now cooling on Castiel's skin, he reaches out to wipe it away.

Lightning-quick, Castiel catches his wrist. "That's mine," he says gently. Dean sucks in a breath.

Castiel lifts his head up from the pillow and kisses Dean's fingertips. "Don't you have a dare to go brag about downstairs?"

***

It's Monday morning and Castiel is strolling down the hallway by the junior lockers, feeling quite on top of the world, thank you very much. It's the kind of glow he's pretty sure you can only get from fucking a mysterious hot stranger whose face you never see and whose name you still don't know...yet. He eyes a cluster of theater kids who are hanging out by the water fountain and mentally crosses them off the list of possibilities, one by one—too short, too tall, too clearly lacking in the ass department.

Sure, he'd spent all weekend jerking off to the memory of Mystery Guy's hips and thighs and mouth and other relevant parts. Sure, going off those memories as he tries to find his Cinderella isn't the most foolproof method, even if they _are_ particularly vivid in his mind. But Castiel isn't worried. He's got a secret weapon. It's hanging around his neck right now. He couldn't believe it when he'd picked it up off his floor the morning after the party, but he's not about to question his good luck.

He crosses the landing and walks past the first of the senior lockers. There's another group of students leaning against the lockers chatting—Castiel thinks he recognizes one of them from the cheerleading squad. He throws them a grin as he passes and one of them—the cheerleader, _ah yes_ , that skirt, of course—twitches, eyes going wide, one hand flying up towards his own chest in an aborted motion that Castiel catches nonetheless.

 _Got you_ , Castiel thinks. He has to work to keep his expression level. His gaze flickers lightning-quick over the cheerleader's frame, taking it in, cataloguing the full lips and freckles and impossibly-long lashes and _god_ , Castiel wants this guy again, right now, up against the lockers, in a bathroom stall, anywhere.

He saunters over. "Hey there."

"Hey, yourself," says one of them, a blonde girl. Cheerleader Guy looks like he's about to pass out.

"I think I've seen you guys around a couple times," says Castiel. "You're on the cheerleading team, right?" He addresses the question at the guy he's ninety percent sure was riding his cock less than seventy-two hours ago. "What's your name?"

Cheerleader Guy's friends have to elbow him before he responds. "Dean," he says faintly, and yes, that voice. Castiel thrills to it. Make that one hundred percent, because he sure as hell remembers that voice moaning, remembers it begging his name. And so help him, he's going to hear his name from that voice again.

"Nice to meet you, Dean," he says.

"I'm Jo, I exist too," says the blonde girl. "This is Benny, Andrea, Charlie." The tiny redhead, the last to be named, is looking back and forth between Castiel and Dean as if watching a tennis match, her face radiant with delight.

"Can't believe we haven't met before," says Castiel easily. "You guys never came to any of my parties?"

Dean looks like he'd like to melt into the lockers, his eyes _so_ very green and his blush _so_ very pink. It's fucking adorable and it makes Castiel want to lean forward and kiss him. Dean's eyes flicker up to meet Castiel's for a second and his tongue darts out to wet his lips, an unconscious gesture that sends heat rushing to pool at the base of Castiel's spine.

"We were never invited," says Jo tartly.

"Well, consider yourselves invited now," says Castiel. "Actually I'm throwing one tonight. Nine p.m." He was planning on doing no such thing, but hey, he's Castiel Novak. What good is it being him if he can't pull together a party on twelve hours' notice?

"We'll definitely be there," says Charlie. Dean shoots her a glare, and she shrugs back at him, her face still split with a mischievous grin.

"Fantastic," says Castiel. He half-turns, then pauses. "Oh, practice is pretty intense this week, there's a slight chance I'll be needing a quick power nap at some point tonight before the party really hits full steam. But if I'm asleep when you get there," he locks eyes with Dean, "just, you know. Make yourselves at home."

And the look in Dean's eyes at that, Castiel thinks as he turns away, is going to be _plenty_ to tide him over until nine p.m.


End file.
